Phosphoric acid salt of beta-bromethyltrimethyl-ammonium-theobromine-1-acetate and process of producing the same



theobromine-l-acetate. The

- is surprising, since Patented Aug. 1, 1933 1,920,697" PHOSPHORIC ACID SALT 0F {i-BROMETHYL- TRIMETHYL-AMMONIUM-THEOBROMINE- OCESS OF PRODUCING l-ACETATE AND PR THE SAME Heinrich Hornstein, Berlin-Halensee, Germany, assignor to Hermann Koch, Berlin, Germany No Drawing. Application May 19, 1932, Serial No. 612,388, and in Germany January 25, 1932 2 Claims. (01. zest-34) This invention relates to a new composition of matter and to the process of producing the same. Object of the present invention is the phosphoric acid salt or 5-bromethyl-trimethyl-ammoniump bromethyltrimethyl-ammonium-theobromine-l-acetate is a salt having strongly hygroscopic properties which impede its employment as a commercial preparation.

It has now been ascertained in accordance with the present invention that, by treating the said salt with phosphoric acid, a compound is obtained that is completely stable in air, convenient to manipulate and unaccompanied by difficulties during storage. According to the experiments performed, the action of the phosphoric acid is based on the formation of a new compound, which forms well-defined crystals and is obtained with an approximately quantitative yield. That phosphoric acid should act in this manner it would be expected that the phosphoric acid would precipitate theobrominel-acetic acid, and that the readily soluble pbromethyl trimethyl would be formed. The new compound has been proved by its'physical and chemical properties to be a chemical entity, and the analysis shows that it contains one theobromine-l-acetic acid residue and one molecule of phosphoric acid to one p-bromethyltrimethylammonium radicle.

A typical method of preparing the compound consists in treating 1 molecule of p-bromethyltrimethylammonium-theobromine l acetatepreferably in the form of a solution or suspension in an organic solventwith 1 molecule of phosphoric acid, preferably in solution in an organic solvent. The new compound crystallizes, almost instantaneously, in well defined massive needles,

and can be further purified by recrystallization.

into the solution ata ammonium phosphate from ethyl or methyl alcohol. It contains 15.9%

of bromine and 18.9% of P04, corresponding to a molecular weight of 502.

' Example I 247 grms. of f3-bromethyltrimethylammoniumbromide (J ahresbericht der Chemie 1858, p. 338) are dissolved in 346 grms. of silver theobromine-l-acetate (Ger. Pat. 524,102) are stirred ing the precipitated silver bromide byflltration, a solution of p-bromethyl-trimethyl-ammoniumtheobromine-l-acetate is obtained.

98 grms. of anhydrous phosphoric acid are dissolved, with cooling, in about 200 grms. of methyl alcohol, and this solution is stirred into the one above. out almost immediately,- down, is filtered at the pump, methyl alcohol and, if desired, from ethyl or methyl alcohol.

1 Example II 404 grms. of 5 -bromethyl-trimethylammonium-theobromine-l-acetate (prepared, as ,se forth in Example 1, par. 1 by double decomposition and concentrating the resulting methanolic solution or precipitating same with ether) are suspended in about 2 litres of acetone, 98 grms. of anhydrous phosphoric acid (also dissolved in acetone) being vigorously stirred into said suspension. The whole sets, after ashort time, to a crystalline pulp of the compound, which is purified in the manner hereinbefore described.

I claim:--

1. A process for the production of the phosphoric acid salt of fl-bromethyltrimethyl-ammonium-theobromine l-acetate, which comprises treating p-bromethyl-trimethyl-ammonium-theobromine-l-acetate with phosphoric acid.

2. The air stable, easily handled and stored phosphoric acid salt of p-bromethyltrimethylammonium-theobromine-l-acetate.

' HEINRICH HORNSTEIN and, after settling washed with recrystallized about a tenfold quantity of methyl alcohol, and

gentle heat. After remov- I The new compound separates 

